866331-13-7

Upstream product

• 866331-12-6 O⁶-methyl-7-deaza-7-nitro-guanine 
• 21740-23-8 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 866331-11-5 N²-isobutyryl-6-chloro-7-deaza-7-nitro-guanine 
• 866331-10-4 N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)isobutyramide 

Downstream Products

• 866331-14-8 3',5'-bis[O-(4-chlorobenzoyl)]-7-deaza-2'-deoxy-7-nitroguanosine 

Relevant academic research and scientific papers

Synthesis and application of nitro-substituted nucleosides and nucleotides

Protocols for the synthesis of C7-nitropurine nucleosides and nucleotides are described. Each of these nucleotides can completely replace its naturally occurring counterpart in polymerase chain reaction (PCR), generating amplified duplex DNA containing nitropurines. As predicted, the electron-withdrawing power of the nitro group rendered these modified oligonucleotides susceptible to chemoselective cleavage at the modified bases. Treatment with secondary amines at elevated temperatures produced selective DNA scission at nitropurine sites. Interestingly, this Maxam-Gilbert type of DNA cleavage reaction was facilitated by the addition of tris(2-carboxyethyl) phosphine (TCEP), a strong reducing agent and nucleophile. Mass spectrometry analysis not only confirmed that DNA cleavage occurred at the nitropurines, but also revealed that the fragmented DNA products are appended by a TCEP moiety at its 3′-end. This surprising result provided new insights into the mechanisms of such DNA cleavage reactions. Georg Thieme Verlag Stuttgart.

Regioselective syntheses of 7-nitro-7-deazapurine nucleosides and nucleotides for efficient PCR incorporation

(Chemical Equation Presented) Substitution at the C7 position of purine nucleotides by a potent electron-withdrawing nitro group facilitates the cleavage of glycosidic bonds under alkaline conditions. This property is useful for sequence-specif